3-[(1-Hydroxy-1-phenylpropan-2-yl)amino]-5,5-dimethylcyclohex-2-enone

The asymmetric unit of the title compound, C17H23NO2, consists of two crystallographically independent molecules (A and B). The cyclohexene rings in both molecules adopt an envelope conformation. In the crystal, independent molecules, A and B, are each linked by intermolecular bifurcated (N,O)—H⋯O hydrogen bonds, generating R 2 1(7) ring motifs and forming infinite chains along the b axis.


1
(7) ring motifs and forming infinite chains along the b axis.

Experimental
A mixture of 5,5-dimethylcyclohexane-1,3-dione (1.4 g, 0.01 mole) and 2-amino-1-phenylpropan-1-ol (1.51 g, 0.01 mole) in dry dimethylformamide (10 ml) containing triethylamine (3 drops) as catalyst was refluxed for 8 h. The obtained solid was recrystallized from ethanol to give the title compound. Single crystals which are suitable for an X-ray structural analysis were obtained by slow evaporation from ethanol at room temperature.

Refinement
Atoms H1NA, H1NB, H1OA and H1OB were located from difference fourier map and refined using a riding model with configuration cannot be determined because the anomalous dispersions are insufficient although Cu radiation was used.
The crystal is not an inversion twin. In the final refinement, 1395 Friedel pairs were merged.

Figure 1
The molecular structure of the title compound with atom labels with 30% probability displacement ellipsoids.

Figure 2
A part of crystal packing of the title compound. The dashed lines represent the hydrogen bonds.  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.